Toward improving the chemistry of N-acyliminium ions: Nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)

Organic Letters

Volumn 7, Issue 14, 2005, Pages 2825-2828

  Othman, Raja Ben ^a   Bousquet, Till ^a   Fousse, Anthony ^a   Othman, Mohamed ^a   Dalla, Vincent ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22244434208     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050576z     Document Type: Article

References (39)

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22. When carefully stored under argon at -20°C, we observed that TIPSOTf could be used with equal success over several months.
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27. Preliminary mechanistic experiments tend to suggest that TIPSOTf does not dissociate and by the way is the real catalyst in the process; more details are given in Supporting Information.
28. The high reactivity of such a stabilized and bulky TIPS silyl enol ether in catalytic α-amido alkylation reactions is unprecedented. Supporting Information gives additional results for various combinations of TIPS enol ethers and N-acyliminium ion precursors to demonstrate further the potential of this new catalytic α-amido alkylation reaction.
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